How CEOs are gambling with $8 million of their own money.

$8 million Gamble
By: Todd Feldman
Founder & President
Rocket Factory

Mid-market CEOs earn gamble an average of $4 million in personal compensation yearly.


It’s widely reported that digital transformation / strategic planning projects fail at a rate of 70-90% of the time, and since it takes at least two years to put a plan into action, those are incredibly bad odds to wait to find out.

Uncovering – and addressing -all of the ways that plans are undermined up front needs to be prioritized. 

At the heart of the pandemic in June 2020, Harvard Business Review published an article entitled “6 Reasons Your Strategy Isn’t Working.” The root of all six reasons all track back to gaps in CEO leadership behavior.

The six reasons are as follows:
    • Unclear values and conflicting priorities
    • An ineffective senior team
    • Ineffective leadership styles
    • Poor coordination
    • Inadequate leadership development
    • Inadequate vertical communication

The unrelenting trifecta

Although McKinsey says (Figure 1) there are six elements and 18 practices that make up the role of a CEO, Rocket Factory analysis has pegged three common themes that drive the greatest pressure:
Changing the way planning is thought of and the way it is executed is in dire need of change. The very livelihoods of the people leaders serve are at stake.
CEO 18 Practices
Figure 1

Beyond the challenges stated above the biggest opportunity falls directly to the behavioral make-up of leaders and how decisions are made.

Adding complexity

Compounding the challenges above are consistently disrupted market forces and the need to focus on being more channel agnostic. Along with that is the need to be more proficient in building sustainable business practices with the right team dynamics.

“I think [leaders] underestimate go-to-market and how complex it is and how complex it’s gotten,” said MJ Patent, Co-Founder and CEO of IT Services strategy firm, Alveo.
“If it’s built on a rocky foundation, or no foundation at all, you’re not getting the maximum value from that investment.”

The ultimate in on-the-job training.

We know that solid planning combined with bold leadership increases the likelihood of earnings success by 6x. And yet, we find that leaders fail to understand their shortcomings and take inventory of how they may be able to improve their chances of success.

Patent said, “[CEOs] have to make very difficult decisions. And if you don’t know the right time to do that, you can shoot yourself in the foot.” There are a lot of leaders that are not trained in it. No one learns how to be a CEO. And if their not of the mindset on how to strengthen that and how those decisions impact the health of the organization things can fall apart from that standpoint.”

Jose Bermejo, CEO of global innovation firm Predictable Innovation, knows the challenges well. “Strategy without execution is nothing. Everything comes down to psychology and the fears that I have, and self-awareness. Accepting what I know and don’t know is the first step to good leadership. Once I accept what I don’t know, new opportunities come up. Because I don’t know what I don’t know, I need to surround myself with other leaders to provide input.”

Stacking the deck

One of the ways to overcome the behavioral challenges that may limit bold strategic leadership and achieving success is for leaders to develop underutilized or undiscovered ways of leading.

To do so requires greater intention to keep up from consistently shifting headwinds.

John Sigmon, a former enterprise Chief Human Resources Officer and CEO of Sigmon Leadership Solutions, has seen firsthand the power of coaching. “I did not always believe in coaching. In fact, I was often dismissive when others would bring up the topic of coaching either for me or as an organizational offering. Quite honestly, I saw coaching as a touchy-feely exercise that offered very little actual value. In the end, it was not the data and science that convinced me. It was the results.”

John’s passion for strong and effective leadership has led him to become a self-proclaimed Leadership Activist. He attributes his success to finding a great coach.

“My entire approach to leadership was turned on its head. My assumptions were challenged, my perspectives questioned, my motivations pulled apart and put back together as my belief system shifted.”

John’s approach has led him to help CEOs explore and develop Zen Leadership’s four key energy patterns that include: Driver, Organizer, Collaborator, and Visionary.

“The challenge is CEOs have found ways to lead that work for them. It’s what got them to where they are in their career. They often ignore other ways to lead. Recognizing other capabilities that they have to lead and exercising them is like an athlete. It takes constant attention and practice. Keeping that aperture open and wide and always asking the question, how can I be more effective?”

Everything’s at stake

We encourage CEOs to reflect deeply on what’s holding them back from strategic success.

From our experience, executive coaching and leadership development is a strategic imperative. And while that may not seem like a new concept, when put directly in the context of a firm’s long-term fortunes – and the livelihoods of those that work there – the picture becomes clear.

With the stakes so high, leaders owe it to everyone involved to explore all ways to mitigate plan failure.